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Talking to Strangers

Updated: Jul 10, 2021

Entrepreneur July/August 2021 “How to Become a Master at Talking to Strangers “Entrepreneurs must become experts at connecting with anyone-and with a few simple strategies, you can. Here’s what happened when I tried them myself” by Joe Keohane who details more in his book “The Power of Strangers:The Benefits of Connecting in a Suspicious World”




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Summary provided by 2244


For various reasons we may avoid striking up chit chat with strangers including it can be “cognitively demanding, tiring, and even stressful” because “you don’t know the person, you don’t know where the conversation is going.” But for the effort some psychologists believe that “talking to a stranger actually boosts your mental performance” and you may find yourself more interesting, more surprising, less loney, and with a larger social and professional network. By connecting more one may feel “joy in it, profundity, [and] real communion.”


How can you improve your conversational skills?


First embrace the simple small talk or chit chat as an opener to a deeper more meaningful conversation. Small talk is “a way to get comfortable with one another” while finding something in common you want to talk about. Openers often start with the weather as a way to bond. “The content is not the point-familiarity, connection, and reassurance are. Once those are in place, a real conversation can happen.”


As you are finding a path to a better conversation you may need to take the first step. Rather than responding to the scripted “How are you?/I’m fine” respond uniquely like I could be better because…. Ultimately a “conversation with no information...goes nowhere.” This way of not generically responding affords the listener to”mirror” because you offered something specific they may follow. A bond is hopefully formed allowing the conversation to “open up.” Other conversation amplifiers might be what would you like to do more of rather than what do you do? In return if you’re lucky, you can get a better idea of the person and a clue to “where you go next in the conversation.” After that, asking an open-ended question, without prying, or better yet making a statement shows active listening, curiosity and demonstrates an “interest in the other person.” Ask that follow-up question and you will be “better liked by...conversational partners.”


“In a good conversation, you must relinquish control. Your job is to help your partner arrive at their own conclusion and surprise you, not to ferret out whatever it is…” You are giving that person "the floor." “If you’re interested only in things you know you’re interested in, you will never be surprised.” “You’ll never learn anything new, or gain a fresh perspective, or make a new friend or contact.”


As the conversation moves along in addition to asking relevant questions be sure to listen actively “make eye contact, and generally show you’re engaged”. The latter can be achieved by “paraphrasing…”it seems like you’re saying…’ and or by simply “echoing” what you heard. Apparently “mimicry...leads to greater liking of the mimicker” and creates rapport.


Types of listening include superficial listening focused on listening for something you know something about-you follow the lead a speaker mentions a known topic say baseball and you add something about baseball. There’s also “listening for information...you show curiosity about someone but your questions are about collecting factual data. You can delve deeper and be a more effective listener by asking Why? How? Who ? etc. Even at this level it’s important to share something about your perspective otherwise the conversation becomes more interrogation.


At the end of the day reaching out will be a mix of connecting well and flopping but with practice one’s confidence, tone and body language will alleviate people’s wariness of conversing with strangers.



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